1. Triple H Defeats The Rock & Big Show & Mick Foley (WrestleMania 2000)
Definitely standing in a class of its own as one of the biggest times a heel would win at WrestleMania, Triple H's victory over not one, but three different opponents angered a fair few fans at the time. WrestleMania 2000 was headlined by 'The Game' defending his WWF Title against The Rock, Mick Foley and The Big Show. There was a McMahon family member in each man's corner, but it would be Stephanie who would be laughing hardest, watching her man come out on top. Unbelievably, Triple H would be the first genuine heel to win in the main event at WrestleMania, 16 events in. A lot of people pointed to this as evidence that the guy was in Vince McMahon's ear, calling the shots, but the truth is that Triple H was a fantastic champion in 2000. Many folks would have likely rather have witnessed The Rock defeat him cleanly in a singles bout at 'Mania, but that would have to wait until Backlash the following month, even if the finish wasn't 100% clean.